Methyl menthol derivative and cooling agent composition containing same

Abstract

The purpose of the present invention is to provide a cooling agent composition containing a novel methyl menthol derivative having no undesirable feeling of stimulation, malodor, bitterness, or the like, it being possible to use the cooling agent composition as a cooling agent or sensory stimulation agent having exceptional persistence of a sense of coolness and refreshing feeling. The present invention pertains to a cooling agent composition containing a methyl menthol derivative represented by general formula (1A) or general formula (1B).

The invention claimed is: 
     
       1. A cooling agent composition, comprising a methyl menthol compound which is selected from the following group: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       2. The cooling agent composition according to  claim 1 , further comprising at least one cool feeling substance other than the methyl menthol compound. 
     
     
       3. The cooling agent composition according to  claim 2 , wherein the cool feeling substance other than the methyl menthol compound is at least one cool feeling substance selected from the group consisting of:
 one or more kinds of compounds selected from menthol, menthone, camphor, pulegol, isopulegol, cineole, cubenol, menthyl acetate, pulegyl acetate, isopulegyl acetate, menthyl salicylate, pulegyl salicylate, isopulegyl salicylate, 3-(1-menthoxy)propan-1,2-diol, 2-methyl-3-(1-menthoxy)propan-1,2-diol, 2-(1-menthoxy)ethan-1-ol, 3-(1-menthoxy)propan-1-ol, 4-(1-menthoxy)butan-1-ol, menthyl 3-hydroxybutanoate, menthyl glyoxylate, p-menthane-3,8-diol, 1-(2-hydroxy-4-methylcyclohexyl)ethanone, menthyl lactate, menthone glycerin ketal, menthyl-2-pyrrolidone-5-carboxylate, monomenthyl succinate, alkali metal salts of monomenthyl succinate, alkaline earth metal salts of monomenthyl succinate, monomenthyl glutarate, alkali metal salts of monomenthyl glutarate, alkaline earth metal salts of monomenthyl glutarate, N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine, p-menthane-3-carboxylic acid glycerol ester, menthol propylene glycol carbonate, menthol ethylene glycol carbonate, p-menthane-2,3-diol, 2-isopropyl-N,2,3-trimethylbutanamide, N-ethyl-p-menthane-3-carboxamide, ethyl 3-(p-menthane-3-carboxamide)acetate, N-(4-methoxyphenyl)-p-menthanecarboxamide, N-ethyl-2,2-diisopropylbutanamide, N-cyclopropyl-p-menthanecarboxamide, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, N-(2-pyridin-2-yl)-3-p-menthanecarboxamide, N-(2-hydroxyethyl)-2-isopropyl-2,3-dimethylbutanamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-diethylbutanamide, cyclopropanecarboxylic acid (2-isopropyl-5-methylcyclohexyl)amide, N-ethyl-2,2-diisopropylbutanamide, N-[4-(2-amino-2-oxoethyl)phenyl]-p-menthanecarboxamide, 2-[(2-p-menthoxy)ethoxy]ethanol, 2,6-diethyl-5-isopropyl-2-methyltetrahydropyran, and trans-4-tert-butylcyclohexanol; 
 one or more sugar alcohols selected from the group consisting of xylitol, erythritol, dextrose, and sorbitol; and 
 one or more natural products selected from the group consisting of Japanese mint oil, peppermint oil, spearmint oil, and  eucalyptus  oil. 
 
     
     
       4. A sensory stimulant composition, comprising the cooling agent composition according to  claim 1 . 
     
     
       5. The sensory stimulant composition according to  claim 4 , further comprising at least one warm feeling substance. 
     
     
       6. The sensory stimulant composition according to  claim 5 , wherein the warm feeling substance is at least one warm feeling substance selected from the group consisting of:
 one or more compounds selected from the group consisting of vanillyl methyl ether, vanillyl ethyl ether, vanillyl propyl ether, vanillyl isopropyl ether, vanillyl butyl ether, vanillyl amyl ether, vanillyl isoamyl ether, vanillyl hexyl ether, isovanillyl methyl ether, isovanillyl ethyl ether, isovanillyl propyl ether, isovanillyl isopropyl ether, isovanillyl butyl ether, isovanillyl amyl ether, isovanillyl isoamyl ether, isovanillyl hexyl ether, ethyl vanillyl methyl ether, ethyl vanillyl ethyl ether, ethyl vanillyl propyl ether, ethyl vanillyl isopropyl ether, ethyl vanillyl butyl ether, ethyl vanillyl amyl ether, ethyl vanillyl isoamyl ether, ethyl vanillyl hexyl ether, vanillin propylene glycol acetal, isovanillin propylene glycol acetal, ethyl vanillin propylene glycol acetal, vanillyl butyl ether acetic acid ester, isovanillyl butyl ether acetic acid ester, ethyl vanillyl butyl ether acetic acid ester, 4-(1-menthoxymethyl)-2-(3′-methoxy-4′-hydroxyphenyl)-1,3-dioxolane, 4-(1-menthoxymethyl)-2-(3′-hydroxy-4′-methoxyphenyl)-1,3-dioxolane, 4-(1-menthoxymethyl)-2-(3′-ethoxy-4′-hydroxyphenyl)-1,3-dioxolane, capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homodihydrocapsaicin, homocapsaicin, biscapsanthin, trishomocapsanthin, nornorcapsanthin, norcapsanthin, capsaicinol, vanillyl caprylamide (octylic acid vanillylamide), vanillyl pelargonamide (nonylic acid vanillylamide), vanillyl caproamide (decylic acid vanillylamide), vanillyl undecamide (undecylic acid vanillylamide), N-trans-feruloyltyramine, N-5-(4-hydroxy-3-methoxyphenyl)-2E,4E-pentadienoylpiperidine, N-trans-feruloylpiperidine, N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoylpiperidine, N-5-(4-hydroxyphenyl)-2E,4E-pentadienoylpiperidine, piperine, isopiperine, chavicine, isochavicine, piperamine, piperettine, piperolein B, retrofractamide A, pipercide, guineenside, piperiline, piperamide C5:1 (2E), piperamide C7:1 (6E), piperamide C7:2 (2E,6E), piperamide C9:1 (8E), piperamide C9:2 (2E,8E), piperamide C9:3 (2E,4E,8E), fagaramide, sanshool-I, sanshool-II, hydroxysanshool, sanshoamide, gingerol, shogaol, zingerone, methylgingerol, paradol, spilanthol, chavicine, polygodial (tadeonal), isopolygodial, dihydropolygodial, and tadeon; and 
 one or more natural products selected from the group consisting of  capsicum  oil,  capsicum  oleoresin, ginger oleoresin, jambu oleoresin ( Spilanthes oleracea  extract), sansho ( Zanthoxylum piperitum ) extract, sanshoamide, black pepper extract, white pepper extract, and  polygonum  extract. 
 
     
     
       7. A flavor composition or a fragrance composition, comprising the sensory stimulant composition according to  claim 4 . 
     
     
       8. A product, which is selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the flavor composition or the fragrance composition according to  claim 7 . 
     
     
       9. A product, which is selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the flavor composition or the fragrance composition according to  claim 7  in an amount of 0.00001 to 50 mass % based on the total weight of the product. 
     
     
       10. A flavor composition or a fragrance composition, comprising the sensory stimulant composition according to  claim 4  in an amount of 0.00001 to 90 mass % based on the total weight of the flavor composition or the fragrance composition. 
     
     
       11. A product, which is selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the sensory stimulant composition according to  claim 4 . 
     
     
       12. A product, which is selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the sensory stimulant composition according to  claim 4  in an amount of 0.00001 to 50 mass % based on the total weight of the product. 
     
     
       13. A method for producing a product, which is selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, wherein the method comprises blending the sensory stimulant composition according to  claim 4 . 
     
     
       14. A method for producing a product, which is selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, wherein the method comprises blending the flavor composition or the fragrance composition according to  claim 7 .